CA2668579A1

CA2668579A1 - Cis-cyclohexyl substituted pyrimidinone derivatives

Cis-cyclohexyl substituted pyrimidinone derivatives Download PDF

Info

Publication number: CA2668579A1
Authority: CA; Canada
Prior art keywords: compound; hydrate; salt; pain; patient
Prior art date: 2006-11-06
Legal status : Abandoned

Application number

CA002668579A

Other languages

English (en)

French (fr)

Inventor

Charles A. Blum

Manuka Ghosh

Isamir Martinez

Xuechun Zhang

Xiaozhang Zheng

Current Assignee

Neurogen Corp

Original Assignee

Individual

Priority date

2006-11-06

Filing date

2007-11-05

Publication date

2008-06-05

2007-11-05 Application filed by Individual filed Critical Individual

2008-06-05 Publication of CA2668579A1 publication Critical patent/CA2668579A1/en

Status Abandoned legal-status Critical Current

Links

VTGOHKSTWXHQJK-UHFFFAOYSA-N pyrimidin-2-ol Chemical class OC1=NC=CC=N1 VTGOHKSTWXHQJK-UHFFFAOYSA-N 0.000 title abstract description 19
150000001875 compounds Chemical class 0.000 claims abstract description 293
238000000034 method Methods 0.000 claims abstract description 67
230000000694 effects Effects 0.000 claims abstract description 65
239000003446 ligand Substances 0.000 claims abstract description 34
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238000011282 treatment Methods 0.000 claims abstract description 29
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238000000338 in vitro Methods 0.000 claims abstract description 21
238000001727 in vivo Methods 0.000 claims abstract description 17
208000002193 Pain Diseases 0.000 claims description 114
230000036407 pain Effects 0.000 claims description 102
108010062740 TRPV Cation Channels Proteins 0.000 claims description 95
239000000203 mixture Substances 0.000 claims description 82
YKPUWZUDDOIDPM-SOFGYWHQSA-N capsaicin Chemical compound COC1=CC(CNC(=O)CCCC\C=C\C(C)C)=CC=C1O YKPUWZUDDOIDPM-SOFGYWHQSA-N 0.000 claims description 77
210000004027 cell Anatomy 0.000 claims description 66
238000003556 assay Methods 0.000 claims description 57
-1 hydroxy, amino Chemical group 0.000 claims description 56
150000003839 salts Chemical class 0.000 claims description 52
125000001424 substituent group Chemical group 0.000 claims description 44
229910052739 hydrogen Inorganic materials 0.000 claims description 43
238000009739 binding Methods 0.000 claims description 40
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RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 27
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OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 claims description 11
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125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims description 6
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